Methanol → HCID 59453924, compound

HRID 1662051Notes

Reaction equation

HRID 1662051 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]1[C:9]([O:11]CC)=[O:10])[CH3:2].CO.C1COCC1.[OH-].[Na+]>O>[CH2:1]([N:3]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]1[C:9]([OH:11])=[O:10])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59454010HCID 59454010, compound

Product 1

HCID 59453924HCID 59453924, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 1-ethyl-4-methyl-1H-pyrrole-2-carboxylate (0.66 g), methanol (5.0 ml), and THF (5.0 ml) was added a 1 M aqueous sodium hydroxide solution (5.0 ml) under ice-cooling, followed by stirring at room temperature for 8.5 days. Water was added to the reaction mixture and the solvent was removed by evaporation under reduced pressure. The residue was washed with diethyl ether, and citric acid was added to the aqueous layer under ice-cooling. The solid precipitated was collected by filtration, washed with water, and dried to obtain 1-ethyl-4-methyl-1H-pyrrole-2-carboxylic acid (0.44 g).

Workup

  1. temperaturecooling
  2. customthe solvent was removed by evaporation under reduced pressure
  3. washThe residue was washed with diethyl ether, and citric acid
  4. additionwas added to the aqueous layer under ice-
  5. temperaturecooling
  6. customThe solid precipitated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-dac7ad255af14cdebfa79ed358a2a322
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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